Top Maine Cruises & Sailing - page 2

Charter a vintage lobster boat, dubbed MONHEGAN, and set sail with this two-hour tour into Casco Bay. You'll get great views of the Maine coastline, passing by four lighthouses as you go. This is a great opportunity to take photos of the coastline and waters, while learning about local nautical history from a knowledgeable captain.

Explore the highlights of Maine's Acadia National Park during this private, half-day guided tour. Get personalized recommendations and information from your tour guide. Cover the Park Loop Road, with panoramic views from Cadillac Mountain—no climbing necessary. Tours include private transfers in a climate-controlled vehicle.

Discover the captivating history of Bar Harbor, Maine, once the summer playground of America’s elite. This self-guided walking tour unveils the rise and fall of this glamorous resort town, where the Vanderbilts and Rockefellers built grand estates along the rugged coastline. With GPS-triggered narration, stroll from Agamont Park to the iconic Bar Island Land Bridge, exploring historic sites, stunning architecture, and hidden stories shaped by both opulence and tragedy. - Self-guided audio tour with GPS navigation for flexibility - Duration of approximately 60–120 minutes—explore at your own pace - Visit landmarks like the Bar Harbor Inn and La Rochelle Mansion - No internet needed; download and go offline for convenience

This is a fully private Southern Maine coastal experience designed exclusively for your party (2–5 guests). No bus groups. No shared travelers — just your group, your pace, and a relaxed day along Maine’s scenic shoreline. Visit historic York’s colonial landmarks, walk through the Old Burying Ground, and enjoy views from John Hancock Wharf before stopping at Cape Neddick Light, one of New England’s most photographed lighthouses. Continue to Ogunquit for time at Perkins Cove, with the option for a short scenic stroll along the Marginal Way overlooking the Atlantic. In Kennebunkport, enjoy unhurried time in Dock Square to browse shops, walk the harbor, and dine at a local restaurant of your choice. A scenic stop at The Colony Hotel adds classic New England charm and sweeping coastal views. Because this tour is private, the experience remains flexible and comfortable, allowing you to explore at your own pace and focus on the scenery and stories that interest you most.

It is the only regularly operating pedicab in Portland. Portland Pedicab creates the feeling of joy for all by allowing passengers to spend the time viewing Portlands scenery while heading to their destination. This is a great mode of transportation for those that like to be outside! Music which is provided, is always an option while enjoying the views of Portland.

Indulge in a private sailing experience along the serene Saco River and Saco Bay. With a maximum of six guests, this exclusive journey allows you to soak in the stunning scenery while learning about the rich history of the area, including the iconic Wood Island Lighthouse and Biddeford Pool. Perfect for all ages, this charter offers a relaxing atmosphere where you can create lasting memories with family and friends amidst the beautiful Maine coastline. Alternative Biddeford Pickup - From Kennebunkport area this location will save 40 minutes of driving.

Wonder at the views from atop of the highest mountain on the eastern seaboard of the United States. From the shore of Sand Beach to the peak of Cadillac Mountain you’ll have the chance to explore the whole 27 miles (43 km) of Acadia’s Park Loop Road. As we meander along shores, coves, cliffs, historic stone bridges, through the woods, and up the mountain, your guide will introduce you to local history, lore, flora, fauna, and geology. You’ll have the opportunity to stop for photos and/or get out to explore as you wish. Sights will included the Wild Gardens of Acadia, Sand Beach, Thunder Hole, Otter Cliffs, Hunters Beach, Jordan Pond, Bubble Pond, Eagle Lake, and Cadillac Mountain Summit. We reserve an extra 30 minutes on every tour so you can relax and not have to watch the clock! Expect your tour guide to be dependable, friendly, and adaptable. We care about your experience on Mount Desert Island! Expect your guide to be knowledgeable and passionate about the Island.

Make the most of your visit to Maine's Acadia National Park during this private, 3-hour guided tour with hotel pickup. Discover top highlights and hidden gems along the Park Loop Road, Otter Cliffs, Thunder Hole, Sand Beach, and more, and enjoy panoramic views from Cadillac Mountain. Tours include bottled water, snacks, entrance fees, and private transfers in a climate-controlled vehicle.

Acadia National Park is as big as it is beautiful, making it simple to get lost when going on your own. Instead, choose this Acadia National Park Self-Guided Driving Audio Tour and see the park’s pristine wilderness while hearing about its history from the safety of your own vehicle. You’ll follow a route through the park on an easy-to-download app that gives recommended speed limits and commentary for a unique experience.

This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special event, or a family get-together that will never be forgotten. Ride aboard Heart's Desire: designed by famed yacht designer - John Alden, measures 53' feet and features some of his trademark design elements including a long bowsprit and dramatic, raked transom. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, and most recently Massachusetts.

Discover the wonders of Acadia with all the sights included in the Sea to Summit tour plus the chance to see so much more of Mount Desert Island! After descending Cadillac Mountain we will head to the one-of-a-kind Somes Sound. We will see more stone bridges, lakes, ponds, streams, cliffs, beaches and coves along the way. You’ll be inspired by the beauty of the Tarn, Hadlock Pond, Eagle Lake, Seal Harbor Beach, Little Long Pond, and the majestic vistas off the cliffs of Cooksey Drive where the rich and famous dwell. You’ll have the opportunity to enjoy the beauty and serenity of Thuya Gardens, and/or Asticou Gardens, before driving the full length of Somes Sound by way of Northeast Harbor. No watching the clock here, we give you extra time to enjoy your day! Expect your tour guide to be dependable, friendly, and adaptable. We care about your experience on Mount Desert Island! Sit back and expect your guide to know exactly where you want to go and what you want to see.

Explore the heart of Portland and head out to see some of the area's hidden gems and less-visited spots with this guided sightseeing tour. Your guide, a born-and-raised Portlander who works as a college librarian by day, shows you off-the-beaten-path locations and shares with you all sorts of local lore along the way.

Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the setting sun bathes the world in mesmerizing hues, crafting memories destined to endure. Set sail along Maine's exquisite coastline aboard our vessel, where every moment unfolds as a cherished tale. Explore the hidden wonders of the Saco River and Saco Bay under the guidance of our seasoned crew. Surrender to the serene embrace of the moment as the ocean murmurs its secrets and the sun paints the horizon with a radiant glow. Seize the opportunity to take the helm and experience the exhilaration of sailing firsthand. Whether craving adventure or seeking inner peace, our private sunset sail promises an unparalleled experience. Allow us to craft an unforgettable journey that lingers in your heart long after the sun has dipped below the horizon. Alternative pickup available in Biddeford for added cost, saves 40 min of driving, contact us for availability.

Discover top sights within Acadia National Park on this 6-hour private tour with your own guide. Cover more locations in less time in a comfortable, air-conditioned vehicle. Highlights include the Park Loop Road, panoramic views from Cadillac Mountain, a stroll through Asticou Gardens, and a lobster lunch stop in Southwest Harbor (meal not included). Hotel pickup is included for added convenience.

Visitors to Portland can easily miss some of Maine's most stunning sights, since you really need a car to explore the scenic coastline. Avoid the headache of arranging your own transportation or renting a car on this small-group guided tour of Portland's must-see sights. Stop in downtown Portland and visit three lighthouses, including Portland Head Light—an historic lighthouse perched on the rocky coast.

Come sailing aboard Heart's Desire, designed by famed yacht designer - John Alden, measures 53' feet and features some of his trademark design elements. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire is 100 years old this year and has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, Massachusetts, and Maine. This two-hour private, morning sail is the perfect way to experience Maine's coastline. Whether you are interested in getting married in an intimate setting, a special way to celebrate a reunion, birthday or anniversary, or just want to enjoy sailing at its finest, step aboard and plan an event never to be forgotten!

Acadia's autumn paints a vibrant scene with fiery hues of red, gold, and russet, reflecting on the calm waters and pink granite cliffs of the Acadia National Park. The air turns crisp, carrying the scent of pine and the whisper of falling leaves. It's a season of beauty and tranquility, a time to witness the wildness of nature transforming into a spectacle of color before the quiet of winter.

Some cities are best seen from a car window. Portland, Maine is not one of them. On this fully private e-bike tour, it's just your group, a local guide, and five hours of spectacular coastal scenery — with a Maine lobster roll along the way. Ride through the Old Port's cobblestone waterfront and fishing piers. Climb to Fort Allen Park for sweeping Casco Bay views. Cruise the Eastern Promenade before crossing to South Portland to walk the breakwater to Bug Light, designed by the architect of the U.S. Capitol dome. Continue to Spring Point Ledge — the only lighthouse of its kind you can reach on foot — then Portland Head Light, commissioned by George Washington in 1791. Finish on the Western Promenade, a hidden hilltop park with views to the White Mountains that most visitors never find. Lunch is a fresh Maine lobster roll at a waterfront spot worthy of the occasion. No strangers, no set pace — just your group and the best of coastal Maine.

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa, a family-run small business charter sailboat, with a coast-guard certified captain, allows you to cruise through Casco Bay, enjoying views of iconic landmarks like Portland Head Light. With options to swim in secluded spots or simply relax, every charter is tailored to your group's preferences. Enjoy light refreshments and the chance to take the helm or trim the sails, making for an unforgettable day on the water.

There are a lot of ways to get out on the water in Maine, but we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and comfortable from the moment you step aboard. A half-day sail is the easiest way to get out on the water and see the Maine coast from a completely different perspective. This small group Maine sailing charter is perfect if you want a relaxed few hours to cruise, take in the views, brush up and your sail trim, or just relax and maybe sneak in a swim on a warm day.

Experience the beauty of coastal Maine on this private guided tour featuring iconic landmarks, scenic harbors, and charming coastal villages. Your journey begins at Portland Head Light, one of the most photographed lighthouses in the United States, where dramatic rocky cliffs and sweeping Atlantic views create unforgettable photo opportunities. From there, travel along Maine’s scenic coastline to the picturesque harbor village of Boothbay Harbor. Walk across the historic Footbridge, built in 1901, and enjoy views of working lobster boats, quiet marinas, and classic New England waterfront scenery. Guests also have the option to enjoy lunch along the harbor at a unique restaurant built from a historic tugboat. With a knowledgeable local guide sharing stories and insights throughout the journey, this private coastal Maine tour offers the perfect blend of history, scenery, and authentic coastal charm.

Set sail with us and immerse yourself in the unparalleled beauty of coastal Maine on our half-day excursion. Traverse the serene waters of the Saco River and Saco Bay with its eight gorgeous islands as you uncover their hidden secrets. If you're intrigued by shipwrecks, daring rescues at sea, or the ghostly hauntings of Wood Island Lighthouse, just let us know – we have a treasure trove of stories to share. Indulge in relaxation as you sip on your favorite beverage and allow us to pamper you with impeccable service. As we sail, keep your eyes peeled for marine wildlife – from playful seals and graceful porpoises to majestic sharks and even whales, every moment on the water promises an encounter with nature's wonders. To ensure an intimate experience, we limit our tours to a maximum of six people. Join us and embark on a journey that will leave you with cherished memories and a newfound love for Maine's breathtaking coastline.

Looking for a romantic way to watch the sunset while in Maine? How about chartering a vintage lobster boat and heading out to Casco Bay, where you'll take in great views of the sea and coastline. Your captain and guide will be on board to point out lighthouses, historic forts, and natural features. A round of drinks is included to toast the sunset with, but more beverages are available to purchase onboard.

There are a lot of ways to get out on the water in Maine, but at Sailing Sasa, we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and comfortable from the moment you step aboard. Every sailing day trip in Maine we offer is fully customizable and built around your group’s vision of a perfect day on the water. Whether we’re exploring the islands, sailing past lighthouses, or anchoring at a secluded cove for a swim, the goal is simple: give you a day that feels easy, personal, and genuinely fun.